Wes Kao

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Asking questions = no skin in the game. If you ask a question, try to answer it

“I asked a smart question. My work here is done!"

Whoa there, not so fast. The hard part is just beginning.

There’s so much dialogue about why it's important to ask questions, but not enough talk about the flip side: why you should answer questions despite working with imperfect information.

When you ask questions, there’s no risk. You can’t be wrong because there’s nothing to be wrong about yet.

Asking a question keeps you at arm’s length. Answering puts you up close.

Asking a question puts the ball in the other person's court. Answering means the ball is in your court.

Asking a question leaves you with lots of options. Answering means making a decision and putting skin in the game.

Questions can't do all the heavy lifting

It’s rare for a question to change everything in an instant.

Most questions don’t part the skies for a holy light to shine through--and that’s okay. Expecting a question to do 100% of the heavy lifting is unrealistic.

Luckily, you don't get rewarded for asking good questions. You get rewarded for creating forward progress.

Sometimes you create progress by asking a question. If you stop there, though, you leave 80% of value on the table. 💰

Think about it: You work with smart people. If it were really so easy to ask one question to change everything, they would have thought of it themselves already.

The problem you're working on is hairy, complicated, and nuanced. Your boss has asked themselves almost every question from different angles.

So it's unlikely that your question will be a mic drop.

That's why the next step will set you apart from everyone else. The next step is helping to answer the question.


There are thousands of ways to answer a question. Which path would you advocate for?


Here are two seemingly simple questions:

"Who is it for?" - This helps you define the target audience for your project.

"What is it for?" - This helps you define what outcome to aim for.

I ask these all the time, and it’s standard for altMBA alumni to constantly ask themselves these questions.

When you try to answer these questions, here's what you'll realize: There are A LOT of ways to answer. And the way you answer literally changes your entire strategy. 😱

"Who is it for" is picking your target audience, which can take months of trial and error.

Let's say you've narrowed down your audience to be "senior executives at tech companies with 50 employees." That sounds pretty well-defined, right? Why would it take trial and error to figure out the "who is it for?"

Because there are still dozens of nuances with the psychographics and worldviews within this group. Which means there are dozens of ways to appeal to them.

Do these senior executives want the proven, standardized choice? Or a radical newcomer? 👨‍💻🤵 <-- That's a Mac vs a PC.

Would your audience respond better if you looked like McKinsey or Glossier? All of those decisions change how you position your offering.

A great product with the wrong audience is going to fail. This is a high-stakes question. Asking it is easy, but answering it is not.

"What is it for?" is about defining what success looks like.

For example, let's say you are debating whether to start a podcast. 🗣

Is your new podcast for generating leads?

For giving you an excuse to reach out to famous people?

For creating an asset that establishes your expertise?

For allowing you to add "Host of the X podcast" to your bio?

Each of these paths changes your strategy, tactics, and metrics. You would measure entirely different things for each.

Asking the question "what is it for?" is easy. But DEFINING your option set and PICKING what to allocate resources towards is hard.


Assert how to fill in the blanks

Questions generate new options. Which is good if you want more options.

But most of us actually want fewer options.

We live in a world where with too many choices and too much data. Most smart people complain about being good at X, Y, Z, and they can't choose what to do.

You don't get rewarded for adding more options to the pile. You get rewarded for bringing wisdom about how to make sense of it all. 🔥

Questions might focus your thinking or redirect your efforts.

But eventually, SOMEONE needs to answer those questions. Someone needs to make assertions about what to do. That someone can be you.

If you don't answer the questions, nothing changes. It's a valuable skill to turn scattered ideas into forward motion.

So the next time you come up with a great question, think about how you would personally answer it. Share your point of view. Advocate for it.

Continue asking questions. But don’t ONLY ask questions.